Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core

Research output: Contribution to journalArticle

Abstract

The synthesis of an unreported 2-aminopyrrolidine-1-carboxamidine unit is here described for the first time. This unusual and promising structure was attained through the oxidative decarboxylation of amino acids using the pair of reagents, silver(I)/peroxydisulfate (Ag(I)/S2O82−) followed by intermolecular (in the case of L-proline derivative) and intramolecular trapping (in the case of acyl L-arginine) by N-nucleophiles. The L-proline approach has a broader scope for the synthesis of 2-aminopyrrolidine-1-carboxamidine derivatives, whereas the intramolecular cyclization afforded by the L-acylarginines, when applied, results in higher yields. The former allowed the first synthesis of cernumidine, a natural alkaloid isolated in 2011 from Solanum cernuum Vell, as its racemic form.

Original languageEnglish
Article number797
JournalMolecules
Volume25
Issue number4
DOIs
Publication statusPublished - 12 Feb 2020

Keywords

  • Amino acid decarboxylation
  • Cernumidine
  • Cyclic-guanidine
  • Radical decarboxylation

Fingerprint Dive into the research topics of 'Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core'. Together they form a unique fingerprint.

Cite this